Asymmetric induction in cyclohexadienones carrying α-D-glucopyranosyl moiety

Saki Yajima, Tsuyoshi Saitoh, Kohei Kawa, Kensuke Nakamura, Hiroshi Nagase, Yasuaki Einaga, Shigeru Nishiyama

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Cyclohexadienone derivatives possessing α-D-glucopyranosyl moiety were designed and synthesized using chemical oxidation or electrochemical oxidation with boron-doped diamond electrode in the final stage. In the chiral induction studies, catalytic hydrogenation provided high diastereoselectivity (dr ratio: > 9:1). Conformational analyses of the C-glucoside structures were performed by NOE experiments and force field calculations, and supported the observed regio-selectivity.

Original languageEnglish
Pages (from-to)8428-8435
Number of pages8
JournalTetrahedron
Volume72
Issue number51
DOIs
Publication statusPublished - 2016

Keywords

  • Anodic oxidation
  • Boron-doped diamond electrodes
  • Cyclohexadienone
  • Diastereoselective hydrogenation
  • Hypervalent iodobenzene

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Yajima, S., Saitoh, T., Kawa, K., Nakamura, K., Nagase, H., Einaga, Y., & Nishiyama, S. (2016). Asymmetric induction in cyclohexadienones carrying α-D-glucopyranosyl moiety. Tetrahedron, 72(51), 8428-8435. https://doi.org/10.1016/j.tet.2016.10.068